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Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester

Active Publication Date: 2018-07-03
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since methanol is toxic and presents a workplace hazard, there is therefore a need to provide fabric softener active compositions comprising tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid esters which compositions have a low content of methanol.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Methanol Content of Commercial Tris-(2-Hydroxyethyl)-Methylammonium Methylsulfate Tallow Fatty Acid Esters

[0031]Table 1 shows methanol contents of commercial tris-(2-hydroxyethyl)-methylammonium methylsulfate tallow fatty acid esters determined by head space GC.

[0032]

TABLE 1Methanol content of commercial tris-(2-hydroxyethyl)-methylammonium methylsulfate tallow fatty acid estersManufacturerProduct nameMethanol content in ppmClariantPraepagen ® TQ7000StepanStepantex ® VA 903300StepanStepantex ® VL 85 G3800StepanStepantex ® VK 903800CognisDehyquart ® AU 466100CognisDehyquart ® AU 575700KaoTetranyl ® AT 14600RewoRewoquat ® V 36203000

example 2

Preparation of Tris-(2-Hydroxyethyl)-Amine Tallow Fatty Acid Ester

[0033]A mixture of 2006 g (6.44 mol) tallow fatty acid having an iodine value of 36 and 632 g (4.26 mol) triethanolamine was heated to 180° C. with stirring, distilling off water from the reaction mixture. After 1 h at this temperature the pressure was reduced stepwise to 10 mbar and the mixture was stirred another 2 h at 180° C. and 10 mbar. The resulting tris-(2-hydroxyethyl)-amine tallow fatty acid ester had an acid value of 7.0 mg KOH / g and a total amine number of 93.7 mg KOH / g.

Preparation of Tris-(2-Hydroxyethyl)-Methylammonium Methyl-Sulfate Tallow Fatty Acid Esters

example 3

Comparative

[0034]111.7 g (0.89 mol) dimethylsulfate was added in small portions with stirring to 563 g (0.94 mol) tris-(2-hydroxyethyl)-amine tallow fatty acid ester from example 2, cooling the reaction mixture to maintain the temperature in the range from 60 to 90° C. After all dimethylsulfate had been added, the reaction mixture was stirred for 1 h at 85° C. Then 75.1 g 2-propanol was added and the mixture was stirred until homogeneous. The resulting composition had a total amine number of 4.6 mg KOH / g and contained 3200 ppm methanol, based on the weight of the composition.

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Abstract

In a method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester by quaternizing a tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate the quaternizing is carried out in the presence of a solid acid scavenger. The method can provide a fabric softener active composition, comprising from 65 to 98% by weight of at least one tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester, the corresponding non-quaternized tris-(2-hydroxyethyl)-amine fatty acid esters in amounts providing a total amine number of the composition of from 2 to less than 7 mg KOH / g, and from 1 to 1500 ppm methanol.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]The present application claims priority to European Application, EP 13191579.5, filed on Nov. 5, 2013, the contents of which is incorporated herein by reference in its entirety.FIELD OF THE INVENTION[0002]The present invention relates to a method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester having a low content of methanol and to fabric softener active compositions obtainable by the method.BACKGROUND OF THE INVENTION[0003]Quaternary ammonium salts carrying two hydrophobic long chain hydrocarbon moieties have found broad use as fabric softener actives. Quaternary ammonium salts of alkanolamines esterified with on average two fatty acid moieties per molecule, commonly referred to as ester quats, have largely replaced earlier alkyl quaternary ammonium compounds because of their biodegradability.[0004]Tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid esters made by quaternizing fatty acid esters...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C305/14C07C219/06C07C213/08C07C305/06C11D3/00C07C219/08C07C303/24C11D3/30C11D3/20C11D1/62
CPCC11D3/001C07C213/08C11D3/30C11D3/201C11D1/62C07C305/06C07C303/24C07C219/06C07C219/08C07C51/412C07C51/48C07C51/493C07C303/40
Inventor KOHLE, HANS-JURGENEULER, AXELSEIDEL, KURTSCHWAB, PETER
Owner EVONIK OPERATIONS GMBH
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